Best of luck on your first deal and here's to many more

In general should I try to stay away from tenant occupied units or if it’s a good deal should I just go for it?  

I would continue looking in the market as good deals do still exist for those willing to do the work.

I want to start getting reps analyzing and underwriting deals that I find.

This way you get the population density that comes with the Chicago area but you don't have to deal with the taxes or the IL eviction laws.

What happens to the deal for the buyer after 3 years and the interest and the loans to you have to be paid? 

I told them deal was off and they need to be out by the 28th of Feb.

@Ricardo SerranoBuild out a team that consist of an investor friendly agent/deal finder, lender, PM, and contractor/handyman.

That would be his issue with his lender.You would have the option of forcing him to complete the deal, he then has to work out the problems between himself and his lender, that is none of your problem or business.Have your attorney or the real estate agent's broker send a strongly worded letter as a warning about the consequences ( a lawsuit he is unlikely to win).

I'm creating these deals in Trusts and brining on equity partners, has anyone done anything like that before?